JP2015519379A5 - - Google Patents
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- JP2015519379A5 JP2015519379A5 JP2015516559A JP2015516559A JP2015519379A5 JP 2015519379 A5 JP2015519379 A5 JP 2015519379A5 JP 2015516559 A JP2015516559 A JP 2015516559A JP 2015516559 A JP2015516559 A JP 2015516559A JP 2015519379 A5 JP2015519379 A5 JP 2015519379A5
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- Prior art keywords
- methyl
- pyridin
- furo
- methanesulfonyl
- trifluoro
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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- 150000003839 salts Chemical class 0.000 claims 9
- 150000001875 compounds Chemical class 0.000 claims 8
- 239000008194 pharmaceutical composition Substances 0.000 claims 4
- -1 diastereomers Chemical class 0.000 claims 2
- 229910052739 hydrogen Inorganic materials 0.000 claims 2
- BAQPWLJKLFPZOJ-UHFFFAOYSA-N 1,1,1-trifluoropropan-2-yl 4-[2-methyl-5-(1-methylsulfonyl-3,6-dihydro-2h-pyridin-4-yl)-3h-furo[2,3-c]pyridin-2-yl]piperidine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)C(F)(F)F)CCC1C1(C)OC2=CN=C(C=3CCN(CC=3)S(C)(=O)=O)C=C2C1 BAQPWLJKLFPZOJ-UHFFFAOYSA-N 0.000 claims 1
- PUKBQZJOQPSPDM-UHFFFAOYSA-N 1,1,1-trifluoropropan-2-yl 4-[5-(1-methylsulfonyl-3,6-dihydro-2h-pyridin-4-yl)-2,3-dihydrofuro[2,3-c]pyridin-2-yl]piperidine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)C(F)(F)F)CCC1C1OC2=CN=C(C=3CCN(CC=3)S(C)(=O)=O)C=C2C1 PUKBQZJOQPSPDM-UHFFFAOYSA-N 0.000 claims 1
- JVAWGGVLLSPWSU-UHFFFAOYSA-N 1,1,1-trifluoropropan-2-yl piperidine-1-carboxylate Chemical compound FC(C(C)OC(=O)N1CCCCC1)(F)F JVAWGGVLLSPWSU-UHFFFAOYSA-N 0.000 claims 1
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims 1
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims 1
- PORGVKHHCKQKHJ-UHFFFAOYSA-N C1CN(C(=O)OC(C)C(F)(F)F)CCC1C1OC2=CN=C(C=3C=CC(=CC=3)S(C)(=O)=O)C=C2C1 Chemical compound C1CN(C(=O)OC(C)C(F)(F)F)CCC1C1OC2=CN=C(C=3C=CC(=CC=3)S(C)(=O)=O)C=C2C1 PORGVKHHCKQKHJ-UHFFFAOYSA-N 0.000 claims 1
- MTGORWSUUZKGAP-UHFFFAOYSA-N CC1(Cc2cc(ncc2O1)-c1ccc(cc1)S(C)(=O)=O)C1CCN(CC1)C(O)=O Chemical compound CC1(Cc2cc(ncc2O1)-c1ccc(cc1)S(C)(=O)=O)C1CCN(CC1)C(O)=O MTGORWSUUZKGAP-UHFFFAOYSA-N 0.000 claims 1
- 102000003688 G-Protein-Coupled Receptors Human genes 0.000 claims 1
- 108090000045 G-Protein-Coupled Receptors Proteins 0.000 claims 1
- BAQPWLJKLFPZOJ-IVZQSRNASA-N [(2r)-1,1,1-trifluoropropan-2-yl] 4-[(2r)-2-methyl-5-(1-methylsulfonyl-3,6-dihydro-2h-pyridin-4-yl)-3h-furo[2,3-c]pyridin-2-yl]piperidine-1-carboxylate Chemical compound C1CN(C(=O)O[C@H](C)C(F)(F)F)CCC1[C@]1(C)OC2=CN=C(C=3CCN(CC=3)S(C)(=O)=O)C=C2C1 BAQPWLJKLFPZOJ-IVZQSRNASA-N 0.000 claims 1
- VGKJXVPMWIUCJY-IQMFZBJNSA-N [(2r)-1,1,1-trifluoropropan-2-yl] 4-[(2r)-2-methyl-5-(4-methylsulfonylphenyl)-3h-furo[2,3-c]pyridin-2-yl]piperidine-1-carboxylate Chemical compound C1CN(C(=O)O[C@H](C)C(F)(F)F)CCC1[C@]1(C)OC2=CN=C(C=3C=CC(=CC=3)S(C)(=O)=O)C=C2C1 VGKJXVPMWIUCJY-IQMFZBJNSA-N 0.000 claims 1
- PUKBQZJOQPSPDM-AUUYWEPGSA-N [(2r)-1,1,1-trifluoropropan-2-yl] 4-[(2r)-5-(1-methylsulfonyl-3,6-dihydro-2h-pyridin-4-yl)-2,3-dihydrofuro[2,3-c]pyridin-2-yl]piperidine-1-carboxylate Chemical compound C1CN(C(=O)O[C@H](C)C(F)(F)F)CCC1[C@@H]1OC2=CN=C(C=3CCN(CC=3)S(C)(=O)=O)C=C2C1 PUKBQZJOQPSPDM-AUUYWEPGSA-N 0.000 claims 1
- PORGVKHHCKQKHJ-JLTOFOAXSA-N [(2r)-1,1,1-trifluoropropan-2-yl] 4-[(2r)-5-(4-methylsulfonylphenyl)-2,3-dihydrofuro[2,3-c]pyridin-2-yl]piperidine-1-carboxylate Chemical compound C1CN(C(=O)O[C@H](C)C(F)(F)F)CCC1[C@@H]1OC2=CN=C(C=3C=CC(=CC=3)S(C)(=O)=O)C=C2C1 PORGVKHHCKQKHJ-JLTOFOAXSA-N 0.000 claims 1
- BAQPWLJKLFPZOJ-OYHNWAKOSA-N [(2s)-1,1,1-trifluoropropan-2-yl] 4-[(2r)-2-methyl-5-(1-methylsulfonyl-3,6-dihydro-2h-pyridin-4-yl)-3h-furo[2,3-c]pyridin-2-yl]piperidine-1-carboxylate Chemical compound C1CN(C(=O)O[C@@H](C)C(F)(F)F)CCC1[C@]1(C)OC2=CN=C(C=3CCN(CC=3)S(C)(=O)=O)C=C2C1 BAQPWLJKLFPZOJ-OYHNWAKOSA-N 0.000 claims 1
- PUKBQZJOQPSPDM-IFXJQAMLSA-N [(2s)-1,1,1-trifluoropropan-2-yl] 4-[(2r)-5-(1-methylsulfonyl-3,6-dihydro-2h-pyridin-4-yl)-2,3-dihydrofuro[2,3-c]pyridin-2-yl]piperidine-1-carboxylate Chemical compound C1CN(C(=O)O[C@@H](C)C(F)(F)F)CCC1[C@@H]1OC2=CN=C(C=3CCN(CC=3)S(C)(=O)=O)C=C2C1 PUKBQZJOQPSPDM-IFXJQAMLSA-N 0.000 claims 1
- PORGVKHHCKQKHJ-VBKZILBWSA-N [(2s)-1,1,1-trifluoropropan-2-yl] 4-[(2r)-5-(4-methylsulfonylphenyl)-2,3-dihydrofuro[2,3-c]pyridin-2-yl]piperidine-1-carboxylate Chemical compound C1CN(C(=O)O[C@@H](C)C(F)(F)F)CCC1[C@@H]1OC2=CN=C(C=3C=CC(=CC=3)S(C)(=O)=O)C=C2C1 PORGVKHHCKQKHJ-VBKZILBWSA-N 0.000 claims 1
- BAQPWLJKLFPZOJ-NYHFZMIOSA-N [(2s)-1,1,1-trifluoropropan-2-yl] 4-[(2s)-2-methyl-5-(1-methylsulfonyl-3,6-dihydro-2h-pyridin-4-yl)-3h-furo[2,3-c]pyridin-2-yl]piperidine-1-carboxylate Chemical compound C1CN(C(=O)O[C@@H](C)C(F)(F)F)CCC1[C@@]1(C)OC2=CN=C(C=3CCN(CC=3)S(C)(=O)=O)C=C2C1 BAQPWLJKLFPZOJ-NYHFZMIOSA-N 0.000 claims 1
- 230000003213 activating effect Effects 0.000 claims 1
- 201000010099 disease Diseases 0.000 claims 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- 230000001404 mediated effect Effects 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 229940124597 therapeutic agent Drugs 0.000 claims 1
- 0 *C(C1)(C(CC2)CCN2C(O*)=O)Oc(cn2)c1cc2[Al] Chemical compound *C(C1)(C(CC2)CCN2C(O*)=O)Oc(cn2)c1cc2[Al] 0.000 description 1
Claims (9)
R1は、少なくとも1個の水素原子がFに置き換わっているC1-4-アルキルから成る群R1-G1より選択され；
Arは下記
LQは、H及びC1-3-アルキルから成る群LQ-G1より選択される）
の化合物、又はその塩。 Formula I
R 1 is selected from the group R 1 -G1 consisting of C 1-4 -alkyl in which at least one hydrogen atom is replaced by F;
Ar is below
L Q is selected from the group L Q -G1 consisting of H and C 1-3 -alkyl)
Or a salt thereof.
LQが、H及びメチルから成る群LQ-G2より選択される、
請求項1に記載の化合物、又はその塩。 R 1 and Ar are as defined in claim 1; and
L Q is selected from the group L Q -G2 consisting of H and methyl,
2. The compound according to claim 1, or a salt thereof.
請求項1又は2に記載の化合物、又はその塩。 R 1 is selected from the group R 1 -G2 consisting of -CH (CH 3 ) (CF 3 ),
The compound according to claim 1 or 2, or a salt thereof.
(a) 4-[5-(4-メタンスルホニル-フェニル)-2,3-ジヒドロ-フロ[2,3-c]ピリジン-2-イル]-ピペリジン-1-カルボン酸2,2,2-トリフルオロ-1-メチル-エチルエステル、
(b) 4-[5-(1-メタンスルホニル-1,2,3,6-テトラヒドロ-ピリジン-4-イル)-2,3-ジヒドロ-フロ[2,3-c]ピリジン-2-イル]-ピペリジン-1-カルボン酸2,2,2-トリフルオロ-1-メチル-エチルエステル、
(c) 4-[5-(1-メタンスルホニル-1,2,3,6-テトラヒドロ-ピリジン-4-イル)-2-メチル-2,3-ジヒドロ-フロ[2,3-c]ピリジン-2-イル]-ピペリジン-1-カルボン酸2,2,2-トリフルオロ-1-メチル-エチルエステル、及び
(d) 4-[5-(4-メタンスルホニル-フェニル)-2-メチル-2,3-ジヒドロ-フロ[2,3-c]ピリジン-2-イル]-ピペリジン-1-カルボン酸2,2,2-トリフルオロ-1-メチル-エチルエステル
から選択される、請求項1に記載の化合物、
そのエナンチオマー、ジアステレオマー、又は塩。 following:
(a) 4- [5- (4-Methanesulfonyl-phenyl) -2,3-dihydro-furo [2,3-c] pyridin-2-yl] -piperidine-1-carboxylic acid 2,2,2- Trifluoro-1-methyl-ethyl ester,
(b) 4- [5- (1-Methanesulfonyl-1,2,3,6-tetrahydro-pyridin-4-yl) -2,3-dihydro-furo [2,3-c] pyridin-2-yl ] -Piperidine-1-carboxylic acid 2,2,2-trifluoro-1-methyl-ethyl ester,
(c) 4- [5- (1-Methanesulfonyl-1,2,3,6-tetrahydro-pyridin-4-yl) -2-methyl-2,3-dihydro-furo [2,3-c] pyridine -2-yl] -piperidine-1-carboxylic acid 2,2,2-trifluoro-1-methyl-ethyl ester, and
(d) 4- [5- (4-Methanesulfonyl-phenyl) -2-methyl-2,3-dihydro-furo [2,3-c] pyridin-2-yl] -piperidine-1-carboxylic acid 2, 2. The compound of claim 1, selected from 2,2-trifluoro-1-methyl-ethyl ester,
Enantiomers, diastereomers, or salts thereof.
(1) (S)-4-[(R)-5-(4-メタンスルホニル-フェニル)-2,3-ジヒドロ-フロ[2,3-c]ピリジン-2-イル]-ピペリジン-1-カルボン酸2,2,2-トリフルオロ-1-メチル-エチルエステル、
(2) (R)-4-[(R)-5-(4-メタンスルホニル-フェニル)-2,3-ジヒドロ-フロ[2,3-c]ピリジン-2-イル]-ピペリジン-1-カルボン酸2,2,2-トリフルオロ-1-メチル-エチルエステル、
(3) (R)-4-[(R)-5-(1-メタンスルホニル-1,2,3,6-テトラヒドロ-ピリジン-4-イル)-2,3-ジヒドロ-フロ[2,3-c]ピリジン-2-イル]-ピペリジン-1-カルボン酸2,2,2-トリフルオロ-1-メチル-エチルエステル、
(4) (S)-4-[(R)-5-(1-メタンスルホニル-1,2,3,6-テトラヒドロ-ピリジン-4-イル)-2,3-ジヒドロ-フロ[2,3-c]ピリジン-2-イル]-ピペリジン-1-カルボン酸2,2,2-トリフルオロ-1-メチル-エチルエステル、
(5) (S)-4-[(S)-5-(1-メタンスルホニル-1,2,3,6-テトラヒドロ-ピリジン-4-イル)-2-メチル-2,3-ジヒドロ-フロ[2,3-c]ピリジン-2-イル]-ピペリジン-1-カルボン酸2,2,2-トリフルオロ-1-メチル-エチルエステル、
(6) (R)-4-[(R)-5-(1-メタンスルホニル-1,2,3,6-テトラヒドロ-ピリジン-4-イル)-2-メチル-2,3-ジヒドロ-フロ[2,3-c]ピリジン-2-イル]-ピペリジン-1-カルボン酸2,2,2-トリフルオロ-1-メチル-エチルエステル、
(7) (S)-4-[(R)-5-(1-メタンスルホニル-1,2,3,6-テトラヒドロ-ピリジン-4-イル)-2-メチル-2,3-ジヒドロ-フロ[2,3-c]ピリジン-2-イル]-ピペリジン-1-カルボン酸2,2,2-トリフルオロ-1-メチル-エチルエステル、
(8) (R)-4-[(R)-5-(4-メタンスルホニル-フェニル)-2-メチル-2,3-ジヒドロ-フロ[2,3-c]ピリジン-2-イル]-ピペリジン-1-カルボン酸2,2,2-トリフルオロ-1-メチル-エチルエステル、及び
(9) (S)-4-[(R)-5-(4-メタンスルホニル-フェニル)-2-メチル-2,3-ジヒドロ-フロ[2,3-c]ピリジン-2-イル]-ピペリジン-1-カルボン酸2,2,2-トリフルオロ-1-メチル-エチルエステル
から選択される、請求項4に記載の化合物、又はその塩。 following:
(1) (S) -4-[(R) -5- (4-Methanesulfonyl-phenyl) -2,3-dihydro-furo [2,3-c] pyridin-2-yl] -piperidine-1- Carboxylic acid 2,2,2-trifluoro-1-methyl-ethyl ester,
(2) (R) -4-[(R) -5- (4-Methanesulfonyl-phenyl) -2,3-dihydro-furo [2,3-c] pyridin-2-yl] -piperidine-1- Carboxylic acid 2,2,2-trifluoro-1-methyl-ethyl ester,
(3) (R) -4-[(R) -5- (1-Methanesulfonyl-1,2,3,6-tetrahydro-pyridin-4-yl) -2,3-dihydro-furo [2,3 -c] pyridin-2-yl] -piperidine-1-carboxylic acid 2,2,2-trifluoro-1-methyl-ethyl ester,
(4) (S) -4-[(R) -5- (1-Methanesulfonyl-1,2,3,6-tetrahydro-pyridin-4-yl) -2,3-dihydro-furo [2,3 -c] pyridin-2-yl] -piperidine-1-carboxylic acid 2,2,2-trifluoro-1-methyl-ethyl ester,
(5) (S) -4-[(S) -5- (1-Methanesulfonyl-1,2,3,6-tetrahydro-pyridin-4-yl) -2-methyl-2,3-dihydro-furo [2,3-c] pyridin-2-yl] -piperidine-1-carboxylic acid 2,2,2-trifluoro-1-methyl-ethyl ester,
(6) (R) -4-[(R) -5- (1-Methanesulfonyl-1,2,3,6-tetrahydro-pyridin-4-yl) -2-methyl-2,3-dihydro-furo [2,3-c] pyridin-2-yl] -piperidine-1-carboxylic acid 2,2,2-trifluoro-1-methyl-ethyl ester,
(7) (S) -4-[(R) -5- (1-Methanesulfonyl-1,2,3,6-tetrahydro-pyridin-4-yl) -2-methyl-2,3-dihydro-furo [2,3-c] pyridin-2-yl] -piperidine-1-carboxylic acid 2,2,2-trifluoro-1-methyl-ethyl ester,
(8) (R) -4-[(R) -5- (4-Methanesulfonyl-phenyl) -2-methyl-2,3-dihydro-furo [2,3-c] pyridin-2-yl]- Piperidine-1-carboxylic acid 2,2,2-trifluoro-1-methyl-ethyl ester, and
(9) (S) -4-[(R) -5- (4-Methanesulfonyl-phenyl) -2-methyl-2,3-dihydro-furo [2,3-c] pyridin-2-yl]- 5. The compound according to claim 4, or a salt thereof, selected from piperidine-1-carboxylic acid 2,2,2-trifluoro-1-methyl-ethyl ester.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP12171686 | 2012-06-12 | ||
| EP12171686.4 | 2012-06-12 | ||
| PCT/EP2013/061653 WO2013186109A1 (en) | 2012-06-12 | 2013-06-06 | 2,3-dihydro-furo[2,3-c]pyridin-2-yl-piperidine derivatives, pharmaceutical compositions containing them and uses thereof |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2015519379A JP2015519379A (en) | 2015-07-09 |
| JP2015519379A5 true JP2015519379A5 (en) | 2016-07-28 |
| JP6119088B2 JP6119088B2 (en) | 2017-04-26 |
Family
ID=48577045
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2015516559A Active JP6119088B2 (en) | 2012-06-12 | 2013-06-06 | 2,3-Dihydro-furo [2,3-c] pyridin-2-yl-piperidine derivatives, pharmaceutical compositions containing them and uses thereof |
Country Status (4)
| Country | Link |
|---|---|
| US (1) | US8975277B2 (en) |
| EP (1) | EP2858996B1 (en) |
| JP (1) | JP6119088B2 (en) |
| WO (1) | WO2013186109A1 (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US9012456B2 (en) * | 2012-02-28 | 2015-04-21 | Boehringer Ingelheim International Gmbh | Compounds, pharmaceutical compositions and uses thereof |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20090221644A1 (en) | 2005-06-30 | 2009-09-03 | Stuart Edward Bradley | Gpcr Agonists |
| US8729084B2 (en) | 2010-05-06 | 2014-05-20 | Bristol-Myers Squibb Company | Benzofuranyl analogues as GPR119 modulators |
| EP2566864B1 (en) * | 2010-05-07 | 2014-09-03 | Boehringer Ingelheim International GmbH | Pyridazinones as gpr119 agonists |
| UY33805A (en) * | 2010-12-17 | 2012-07-31 | Boehringer Ingelheim Int | ? Dihydrobenzofuranyl-piperidinyl, aza-dihydrobenzofuranylpiperidinyl and diaza-dihydrobenzofuranyl-piperidinyl derivatives, pharmaceutical compositions containing them and uses thereof? |
-
2013
- 2013-06-06 JP JP2015516559A patent/JP6119088B2/en active Active
- 2013-06-06 US US13/911,138 patent/US8975277B2/en active Active
- 2013-06-06 WO PCT/EP2013/061653 patent/WO2013186109A1/en not_active Ceased
- 2013-06-06 EP EP13727170.6A patent/EP2858996B1/en active Active
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